Triisopropyl phosphite → HCID 54076214, compound

HRID 376102Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH:16][CH:17]=[O:18])[CH:6]=[C:7]([CH2:14]Br)[CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH3:2].[P:20]([O:29]C(C)C)([O:25][CH:26]([CH3:28])[CH3:27])[O:21][CH:22]([CH3:24])[CH3:23]>>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([NH:16][CH:17]=[O:18])[CH:6]=[C:7]([CH2:14][P:20]([O:25][CH:26]([CH3:28])[CH3:27])([O:21][CH:22]([CH3:24])[CH3:23])=[O:29])[CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH3:2]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 54470496HCID 54470496, compound

Product 1

HCID 54076214HCID 54076214, compound

Procedure

8.7 g (25 mmol) of 6-acetoxy-4-bromomethyl-2-formylamino-hex-3-enoic acid ethyl ester and 21 ml (75 mmol) of triisopropyl phosphite (90%) are heated to from 80° to 90° C. and stirred for 19 hours under a pressure of approximately 100 mbar. The excess triisopropyl phosphite is distilled off and the evaporation residue is chromatographed on 150 g of silica gel with first ethyl acetate and then ethyl acetate/ethanol (9: 1) as eluants. 6-acetoxy-4-diisopropylphosphonomethyl-2-formylamino-hex-3-enoic acid ethyl ester is obtained in the form of a yellowish oil.

Workup

distillationThe excess triisopropyl phosphite is distilled off
customthe evaporation residue is chromatographed on 150 g of silica gel with first ethyl acetate

Sources & evidence

ORD record: ord-63f803bc2aab4b3fb81170553392e931
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488140

Reaction notes

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